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Visible‐Light‐Mediated Regioselective Allylation, Benzylation, and Silylation of Methylene‐Malononitriles via Photoredox‐Induced Radical Cation Fragmentation
Author(s) -
Liu Rongfang,
Chia Shane Pui Mun,
Goh Yi Yiing,
Cheo Han Wen,
Fan Binbin,
Li Ruifeng,
Zhou Rong,
Wu Jie
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900902
Subject(s) - regioselectivity , chemistry , silylation , allylic rearrangement , photochemistry , methylene , radical , reagent , fragmentation (computing) , photoredox catalysis , medicinal chemistry , organic chemistry , catalysis , photocatalysis , computer science , operating system
Visible‐light‐mediated regioselective allylation, benzylation, and silylation of methylene‐malononitriles using allylic/benzylic silane and disilane reagents have been developed, delivering the corresponding allylated, benzylated, and silylated products in moderate to excellent yields. These reactions proceed smoothly with exclusive regioselectivity by employing only an organo‐photoredox catalyst under very mild conditions. A photoredox‐induced radical cation fragmentation is proposed for the generation of the key allylic, benzylic, and silyl radicals.